A convenient approach towards boron cluster modifications with adenosine and 2′-deoxyadenosine

New 2′-deoxyadenosine and adenosoine modifications: 8-[(2-dimethylaminoethyl)amino]-2′-deoxyadenosine and 8-[(2-dimethylaminoethyl)amino]adenosine were prepared and their reactivity towards cyclic oxonium adducts of closo-dodecaborate and cobalt-bis-dicarbollide was studied. The cleavage reactions of clusters oxonium rings by N,N-dimethylanio group of modified nucleosides led to the first [B12H12]2− and new [Co(C2B9H11)2]− conjugates with adenosine and 2′-deoxyadenosine respectively. The proposed methodology provides a convenient route for the synthesis of libraries of boron cluster modified adenosine and 2′-deoxyadenosine derivatives for biological screening.

Graphical abstractReactions of novel nucleoside (8-[(2-dimethylaminoethyl)amino]-20-deoxyadenosine and adenosine) with oxonium adducts of closo-dodecaborate and cobalt-bis(dicarbollide) were studied and have given rise to the synthesis of the first [B12H12]2− and [Co(C2B9H11)2]− conjugates. The proposed methodology provides a convenient route for the synthesis of libraries of boron modified nucleosides derivatives for biological screening.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► A new effective route for boron cluster-based deoxy/adenosines was developed. ► New 8-modified Ado and dAdo with nucleophilic centre were prepared. ► Using these reagents, conjugates of [B12H12]2− and [Co(C2B9H11)2]− were synthesized.